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I asked PostSecret followers on facebook for once-in-a-lifetime questions to ask my dad for an unforgettable interview. Over 700 replies with more than 1,000 questions came back.

This was my original post:

I was thrilled with all the thoughtful questions you shared with me, from the delightful to the profound. I read all of them and picked 25 to ask my dad. At a family dinner the night before our day of tandem paragliding, as an experiment, I peppered three into our conversation. . . it didn’t go well.

Like many families, ours was far from perfect, with divorce and estrangement being a part of it. So when other family members began responding to some of my father’s answers, long-buried feelings and some judgement turned the interview sour. Because of that learning experience, I changed some of my questions and gained three insights for when I would try again the next day.

• Avoid questions about regrets or mistakes and start with questions that include the word “favorite”, like, What’s your favorite decade and why?
• Keep the questions open-ended and let answers lead to other answers. Aim for a flowing conversation, not an interview.
• Really listen.

On the two hour drive to the Gliderport the next day, it was just my father and me in the car. I told him how much it meant to me to go through these questions and get to know him better. He was game so I cautiously started. He passed on some of the questions, but then really began to share a lot with me, including a secret. He even started asking me some of the same questions too! The spirit in the car was supportive and generous, with some heartfelt laughs as we used questions as prompts for our once-in-a-lifetime conversation.

Even though we were unable to do any gliding because of wind conditions, I’ll never forget that day and the new appreciation I have for me father. I can’t reveal the secret he told me but another part of our conversation shocked me. I asked this gentle and caring man, what is the most common misconception people have about you? He said. When I was ten-years-old, my mom spanked me for the last time. I don’t think you know how stubborn I was then but you do know how stern your Grandmother could be. I remember through my tears and pain looking at my mother and saying, with spite, “I like getting spanked”!

Here are the 25 questions that guided our conversation with some additional resources at the bottom.

~~~

Can you tell me about your best friend when you were a kid and one of your adventures.

What is the oldest story you know about our ancestors?

Is there something about me that you have always wanted to know but have never asked?

Can you describe a favorite memory about a family member?

If this was to be our very last conversation, is there anything you would want to say to me?

Do you have a favorite snack, song, television show, recipe, comedy?

What is your first memory?

Did you ever get into trouble as a kid? What happened?

If there was a biography of you, how would you want to be described?

What choice are you thankful that you did not make?

What is the best advice you remember from your father?

Is there anything you wish you had said to someone but didn’t have the chance?

Can you teach me something?

What is something you would like me to ask you?”

What do you wish you would have spent less time worrying about?

What is something you deliberately did not tell me as a child and why?

What is the best part of your day? What makes you feel most alive?

What is the last thing you changed your mind about?

What things helped you get through a difficult time in your life?

Over the course of your life what trip or place was most special? Why?

What would you like to re-experience again because you did not appreciate it enough the first time?

Can you tell me something about yourself that I don’t know that you think would surprise, shock or delight me?

What habits served you the most through life?

What is the best mistake you have made, and why?

What do you hope my siblings and I have learned from you?

How are you doing right now? Is there anything on your mind right now that you’d like to talk about?

~~~

(When my father visits again, I’ll be sure to have his favorite comedy and snack ready.)

~~~

Thank You, to everyone in the PostSecret community who has donated their money or time to suicide prevention. As someone who has answered those phones on the overnight shift, I can tell you, There Is Hope And There Is Help.

In the early aughts, Frank Warren ran a medical document delivery business in Germantown, Maryland. It was a monotonous job, involving daily trips to government offices to copy thousands of pages of journal articles for pharmaceutical companies, law firms, and non-profits. By his early forties, he had a house in a nice subdivision, a wife, a young daughter, and a dog. His family fostered children for a few weeks or months, and he felt a sense of purpose in helping kids who were suffering acute crises in their own homes. From the outside, things appeared to be going better than well. But inside, something was missing: A sense of adventure, or at least a little fun. An outlet to explore the weirder, darker, and more imaginative parts of his interior world. He’d never been one for small talk, preferring instead to launch into deep discussions, even with people he barely knew. He wondered if he could create a place like that outside of everyday conversation, a place full of awe, anguish, and urgency.

In the fall of 2004, Frank came up with an idea for a project. After he finished delivering documents for the day, he’d drive through the darkened streets of Washington, D.C., with stacks of self-addressed postcards—three thousand in total. At metro stops, he’d approach strangers. “Hi,” he’d say. “I’m Frank. And I collect secrets.” Some people shrugged him off, or told him they didn’t have any secrets. Surely, Frank thought, those people had the best ones. Others were amused, or intrigued. They took cards and, following instructions he’d left next to the address, decorated them, wrote down secrets they’d never told anyone before, and mailed them back to Frank. All the secrets were anonymous.

Initially, Frank received about one hundred postcards back. They told stories of infidelity, longing, abuse. Some were erotic. Some were funny. He displayed them at a local art exhibition and included an anonymous secret of his own. After the exhibition ended, though, the postcards kept coming. By 2024, Frank would have more than a million.

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